Verified Review icon check navigate-up navigate-left navigate-right expand mail svg-lightning svg-24hr svg-house svg-sleeps svg-bedrooms svg-bathrooms svg-stay svg-toilet calendar svg-report-flag pet-dog svg-multiunit Default Owner Icon heart-filled Family icon
Cancel Clear Filters Apply Filters
More Filters

Price Per Night

$ $

Bedrooms

Bathrooms

Booking Options

Property Type

Location Type

Even More Filters

Features

Managed By

Clear Filters
Use filters to narrow your search results!
Viewed 26 times in the last 48 hours
  • 4 BR
  • 2 BA
  • 1 HF BA
  • 2400 sq. ft.
Wonderful! 4.9/5
(20 reviews)
avg/night
House #223906
20
Viewed 10 times in the last 48 hours
  • 3 BR
  • 2 BA
  • 2100 sq. ft.
Wonderful! 4.9/5
(8 reviews)
View details for price
House #840127
8
Viewed 22 times in the last 48 hours
  • 3 BR
  • 1 BA
  • 800 sq. ft.
avg/night
Cottage #472272
4
Viewed 37 times in the last 48 hours
  • 4 BR
  • 2 BA
  • 1 HF BA
  • 2100 sq. ft.
Wonderful! 4.9/5
(13 reviews)
avg/night
House #679747
13
Viewed 51 times in the last 48 hours
  • 2 BR
  • 1 BA
  • 800 sq. ft.
Exceptional! 5/5
(1 reviews)
$40
avg/night
House #112239ha
1
  • 2 BR
  • 2 BA
  • 1200 sq. ft.
Excellent! 4.6/5
(5 reviews)
avg/night
Cottage #580958
5
Viewed 41 times in the last 48 hours
  • 5 BR
  • 3 BA
  • 2400 sq. ft.
Excellent! 4.7/5
(12 reviews)
avg/night
House #980094ha
12
Viewed 22 times in the last 48 hours
  • 4 BR
  • 4 BA
  • 2500 sq. ft.
Excellent! 4.7/5
(15 reviews)
avg/night
Estate #559364
15
Viewed 32 times in the last 48 hours
  • 2 BR
  • 1 BA
  • 960 sq. ft.
avg/night
House #1220493
Viewed 36 times in the last 48 hours
  • 3 BR
  • 2 BA
  • 1200 sq. ft.
avg/night
House #4506394ha
3
Viewed 25 times in the last 48 hours
  • 3 BR
  • 2 BA
  • 1 HF BA
  • 1784 sq. ft.
Exceptional! 5/5
(9 reviews)
avg/night
House #3708573ha
9
Viewed 5 times in the last 48 hours
  • 3 BR
  • 2 BA
Excellent! 4.6/5
(5 reviews)
avg/night
House #454191
5
  • 5 BR
  • 2 BA
  • 1700 sq. ft.
avg/night
Cottage #3959151ha
1
Viewed 17 times in the last 48 hours
  • 3 BR
  • 2 BA
  • 1400 sq. ft.
Exceptional! 5/5
(6 reviews)
avg/night
House #293733ha
6
Viewed 32 times in the last 48 hours
Premier Partner
  • 4 BR
  • 2 BA
  • 3081 sq. ft.
Very Good! 4.1/5
(7 reviews)
avg/night
Apartment #720739
7
Viewed 17 times in the last 48 hours
  • 4 BR
  • 3 BA
  • 2500 sq. ft.
Exceptional! 5/5
(10 reviews)
avg/night
House #131517ha
10
  • 3 BR
  • 2 BA
avg/night
Cottage #3779593ha
2
Viewed 16 times in the last 48 hours
  • 1 BR
  • 1 BA
avg/night
Cottage #375598
1
Viewed 34 times in the last 48 hours
  • 3 BR
  • 1 BA
  • 1 HF BA
Exceptional! 5/5
(13 reviews)
avg/night
House #371811
13
Viewed 5 times in the last 48 hours
  • 2 BR
  • 2 BA
  • 1400 sq. ft.
Exceptional! 5/5
(16 reviews)
avg/night
House #174495
16
Viewed 36 times in the last 48 hours
  • 3 BR
  • 1 BA
  • 800 sq. ft.
avg/night
Cottage #4052295ha
Viewed 35 times in the last 48 hours
  • 5 BR
  • 2 BA
  • 3000 sq. ft.
avg/night
House #1011987
4
Viewed 15 times in the last 48 hours
  • 4 BR
  • 2 BA
  • 1 HF BA
  • 2352 sq. ft.
avg/night
House #4746168ha
Viewed 19 times in the last 48 hours
  • 3 BR
  • 2 BA
  • 2400 sq. ft.
avg/night
House #4165995ha
2
Viewed 19 times in the last 48 hours
  • 3 BR
  • 1 BA
  • 1200 sq. ft.
Wonderful! 4.8/5
(9 reviews)
avg/night
House #568907
9
  • 4 BR
  • 1 BA
  • 1 HF BA
  • 1250 sq. ft.
Exceptional! 5/5
(11 reviews)
avg/night
House #3932081ha
11
Viewed 31 times in the last 48 hours
  • 3 BR
  • 2 BA
  • 1 HF BA
  • 2700 sq. ft.
Wonderful! 4.9/5
(11 reviews)
$73
avg/night
House #505692
11
  • 3 BR
  • 3 BA
  • 1 HF BA
  • 2000 sq. ft.
avg/night
House #4466657ha
1
  • 4 BR
  • 2 BA
  • 2 HF BA
  • 3500 sq. ft.
Exceptional! 5/5
(21 reviews)
avg/night
House #329587
21
  • 4 BR
  • 3 BA
avg/night
House #182266ha
3
Viewed 13 times in the last 48 hours
  • 5 BR
  • 3 BA
  • 1 HF BA
avg/night
House #1033086
2
Viewed 7 times in the last 48 hours
  • 3 BR
  • 2200 sq. ft.
Exceptional! 5/5
(6 reviews)
avg/night
House #956719ha
6
Viewed 19 times in the last 48 hours
  • 5 BR
  • 3 BA
  • 1 HF BA
  • 2000 sq. ft.
Excellent! 4.7/5
(6 reviews)
avg/night
House #3813604ha
6
Viewed 10 times in the last 48 hours
Premier Partner
  • 4 BR
  • 2 BA
  • 1684 sq. ft.
avg/night
House #922593
2
Viewed 50 times in the last 48 hours
Premier Partner
  • 4 BR
  • 4 BA
  • 2500 sq. ft.
Exceptional! 5/5
(5 reviews)
avg/night
House #883157
5
Viewed 7 times in the last 48 hours
  • 2 BR
  • 1 BA
  • 1000 sq. ft.
avg/night
Cottage #874121
3
Viewed 13 times in the last 48 hours
  • 4 BR
  • 3 BA
  • 3100 sq. ft.
Exceptional! 5/5
(5 reviews)
avg/night
House #136112ha
5
Viewed 32 times in the last 48 hours
  • 4 BR
  • 4 BA
  • 3400 sq. ft.
avg/night
House #661040
2
Viewed 11 times in the last 48 hours
  • 4 BR
  • 3 BA
  • 2500 sq. ft.
avg/night
House #240371ha
Viewed 12 times in the last 48 hours
  • 4 BR
  • 3 BA
  • 2 HF BA
  • 1872 sq. ft.
Exceptional! 5/5
(10 reviews)
avg/night
House #837823
10
Viewed 25 times in the last 48 hours
  • 4 BR
  • 3 BA
  • 2400 sq. ft.
Exceptional! 5/5
(10 reviews)
avg/night
House #704051
10
Viewed 16 times in the last 48 hours
  • 4 BR
  • 2 BA
  • 1 HF BA
  • 2310 sq. ft.
avg/night
House #1101066
Viewed 11 times in the last 48 hours
  • 3 BR
  • 1 BA
  • 1 HF BA
  • 1800 sq. ft.
Exceptional! 5/5
(6 reviews)
avg/night
House #813766
6
Viewed 5 times in the last 48 hours
  • 2 BR
  • 1 BA
  • 1 HF BA
  • 1665 sq. ft.
avg/night
House #151143ha
4
Viewed 54 times in the last 48 hours
  • 5 BR
  • 4 BA
  • 3500 sq. ft.
avg/night
House #41681
2
Viewed 6 times in the last 48 hours
  • 5 BR
  • 2 BA
Exceptional! 5/5
(1 reviews)
avg/night
House #415177
1
Viewed 5 times in the last 48 hours
  • 2 BR
  • 1 BA
  • 1 HF BA
  • 1700 sq. ft.
avg/night
House #715165
3
Viewed 19 times in the last 48 hours
  • 5 BR
  • 1 BA
  • 1 HF BA
Exceptional! 5/5
(7 reviews)
avg/night
House #216987
7
Viewed 8 times in the last 48 hours
  • 4 BR
  • 3 BA
avg/night
Barn #898821
  • 3 BR
  • 2 BA
  • 2000 sq. ft.
avg/night
House #1052728
2
 

Recent Chilmark Reviews

Wonderful vacation retreat

5 of 5
Lovely comfortable home in a great location. Kitchen is well appointed for those who like to cook. Enjoy a quiet, relaxing space, spacious deck, and cozy comforts.
  • Submitted: Nov 30, 2017
  • Stayed: Nov 2017

Weathering the Storm on Old County Road

5 of 5
I arrived at this lovely house in time for a visit from Jose...wind, rain, no sunshine, no boats to take my friends home. Very disappointing weather but that's how it goes sometimes. Staying in this house made it all bearable. The furnishings are comfortable but not fussy. The kitchen was well-stocked with utensils for those who really like to cook and it was pristine. The location is perfect if you love up-Island life. It was so quiet but not Spooky. The family that owns the house lives nearby and their daughter Colleen was such a gracious host. I hope to rent this home again next year.
  • Submitted: Sep 25, 2017
  • Stayed: Sep 2017